tert-butyl N-(5-(tributylstannyl)-1,3-thiazol-2-yl)carbamate → tert-Butyl 5-(cinnolin-6-yl)thiazol-2-ylcarbamate

HRID 661124Notes

Reaction equation

HRID 661124 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[N:7][CH:6]=[CH:5]2.C([Sn](CCCC)(CCCC)[C:17]1[S:21][C:20]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[N:19][CH:18]=1)CCC>>[N:8]1[C:9]2[C:4](=[CH:3][C:2]([C:17]3[S:21][C:20]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[N:19][CH:18]=3)=[CH:11][CH:10]=2)[CH:5]=[CH:6][N:7]=1

Participants

3

Reactant 2

HCID 2763269tert-butyl N-(5-(tributylstannyl)-1,3-thiazol-2-yl)carbamateHCID 112295606-Bromocinnoline

Product 1

HCID 86613781tert-Butyl 5-(cinnolin-6-yl)thiazol-2-ylcarbamateYield 73.1%

Procedure

The title compound (0.24 g, 60%) was synthesized in a manner similar to that described in Example 253 from 6-bromocinnoline (0.25 g, 1.0 mmol) and tert-butyl 5-(tributylstannyl)thiazol-2-ylcarbamate (0.90 g, 1.5 eq). LCMS (API-ES) m/z (%): 329.4 (100%, M++H).

Sources & evidence

ORD record
ord-4965d1383b964c8f9eae123414ee8795
Source dataset
uspto-grants-2011_12
Patent number
US08084479B2

Reaction notes

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